American Airlines flights from Chicago to San Jose, CR

Recent searches for flights from Chicago to San Jose, CR

Aug 2026
From$505*
Updated: 4 hours ago
Round tripIEconomy
Sep 2026
From$483*
Updated: 4 hours ago
Round tripIEconomy
Oct 2026
From$378*
Updated: 4 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $483
cmp-daily-histogram-bars-legend-max-price-aria-label $1.0K
Displaying fares for August-2026
  • ORD–SJO, 08/23/26 – 08/30/26: From $779
    23

    Su

    AUG

  • ORD–SJO, 08/24/26 – 08/31/26: From $774
    24

    Mo

  • ORD–SJO, 08/25/26 – 09/01/26: From $774
    25

    Tu

  • ORD–SJO, 08/26/26 – 09/02/26: From $664
    26

    We

  • ORD–SJO, 08/27/26 – 09/03/26: From $637
    27

    Th

  • ORD–SJO, 08/28/26 – 09/04/26: From $530
    28

    Fr

  • ORD–SJO, 08/29/26 – 09/05/26: From $597
    29

    Sa

  • ORD–SJO, 08/30/26 – 09/06/26: From $505
    30

    Su

  • ORD–SJO, 08/31/26 – 09/07/26: From $525
    31

    Mo

  • ORD–SJO, 09/01/26 – 09/08/26: From $613
    01

    Tu

    SEP

  • ORD–SJO, 09/02/26 – 09/09/26: From $970
    02

    We

  • ORD–SJO, 09/03/26 – 09/10/26: From $632
    03

    Th

  • ORD–SJO, 09/04/26 – 09/11/26: From $827
    04

    Fr

  • ORD–SJO, 09/05/26 – 09/12/26: From $1,034
    05

    Sa

  • ORD–SJO, 09/06/26 – 09/13/26: From $572
    06

    Su

  • ORD–SJO, 09/07/26 – 09/14/26: From $567
    07

    Mo

  • ORD–SJO, 09/08/26 – 09/15/26: From $567
    08

    Tu

  • ORD–SJO, 09/09/26 – 09/16/26: From $588
    09

    We

  • ORD–SJO, 09/10/26 – 09/17/26: From $500
    10

    Th

  • ORD–SJO, 09/11/26 – 09/18/26: From $500
    11

    Fr

  • ORD–SJO, 09/12/26 – 09/19/26: From $500
    12

    Sa

  • ORD–SJO, 09/13/26 – 09/20/26: From $593
    13

    Su

  • ORD–SJO, 09/14/26 – 09/21/26: From $483
    14

    Mo

  • ORD–SJO, 09/15/26 – 09/22/26: From $669
    15

    Tu

  • ORD–SJO, 09/16/26 – 09/23/26: From $588
    16

    We

  • ORD–SJO, 09/17/26 – 09/24/26: From $588
    17

    Th

  • ORD–SJO, 09/18/26 – 09/25/26: From $588
    18

    Fr

  • ORD–SJO, 09/19/26 – 09/26/26: From $588
    19

    Sa

  • ORD–SJO, 09/20/26 – 09/27/26: From $593
    20

    Su

  • ORD–SJO, 09/21/26 – 09/28/26: From $588
    21

    Mo

  • ORD–SJO, 09/22/26 – 09/29/26: From $588
    22

    Tu

    • range$483-$1,034

    DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on Chicago to San Jose, CR flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    San Jose, CR (SJO)
    10/24/26 - 10/31/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    San Jose, CR (SJO)
    10/29/26 - 11/05/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    San Jose, CR (SJO)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    San Jose, CR (SJO)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    San Jose, CR (SJO)
    10/14/26 - 10/21/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    San Jose, CR (SJO)
    10/19/26 - 10/26/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    San Jose, CR (SJO)
    11/13/26 - 11/20/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    Chicago (ORD)to

    San Jose, CR (SJO)
    11/14/26 - 11/21/26

    Round trip

    Economy

    from
    $378Fare subject to changes
    Updated: 4 hours ago

    *Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

    Finding cheap flights from Chicago to San Jose, CR

    Looking for lower fares on your trip from Chicago to San Jose, CR? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Chicago to San Jose, CR